Winona vacation rentals

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Top-rated vacation rentals in Winona

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Farm stay in Dakota

4.93 out of 5 average rating, 246 reviews

The Bungalow at Heart and Soil Ridge

Welcome to Heart and Soil Ridge! Come experience life on a Minnesota farm nestled in the rolling hills of the Driftless region. Relax out on the deck, swing in a hammock among the trees, or enjoy a walk through our beautiful cover crop fields. This is a working farm and depending on the season, you are welcome to help collect eggs, observe the farm animals, learn about regenerative agriculture, and visit our Fox Red labradors. We want your experience at our farm to be relaxing and refreshing!

Feb 27 – Mar 6

R1,675 ZAR per night

Guest favorite

Home in Minnesota City

4.98 out of 5 average rating, 272 reviews

✨Vintage Lustron Home✨

Enjoy a stay in this vintage Lustron Home. It is a unique home. It has two bedrooms, and a sofa sleeper in the living room. The master bedroom has a queen size bed. The second bedroom has two twin beds. This home offers a washer and dryer for your convenience. It has a large fenced yard to enjoy during your stay. Off street parking and Wi-Fi included. This home is in a very peaceful neighborhood. Located close to Winona State University and St. Mary's University. There are State Parks close also

Sep 19 – 26

R2,115 ZAR per night

Guest favorite

Tiny home in Black River Falls

4.98 out of 5 average rating, 335 reviews

Tiny on the River

According to Forbes, Escape makes "the most beautiful tiny houses in the world". Ours is perched near our home above the Black River. It's a quiet neighborhood just minutes from the interstate, parks, trails, and our vibrant downtown with cafés, shops, and great restaurants. Enjoy privacy and breathtaking views from the enormous windows or the cozy daybed on the porch! Deer, beaver, eagles, and more make frequent cameos as the seasons paint shifting riverscapes and astonishing sunsets. *No Pets

Oct 24 – 31

R3,071 ZAR per night

Guest favorite

Apartment in Winona

4.94 out of 5 average rating, 139 reviews

Cozy & Bright 2nd Floor Apt - 7 Blocks from WSU

Our newly-remodeled one-bedroom apartment is the perfect getaway for two guests. * Spacious bedroom with queen size bed, couch and workspace * Hardwood floors throughout * Full kitchen with oven, refrigerator, microwave + coffee/tea station * Walking distance to WSU and Cotter * Located on the 2nd floor with off-street parking * Your own washer dryer in the apartment * Easy self-check-in process We want you to love your time in Winona and are here to make your stay as pleasant as possible.

Oct 27 – Nov 3

R1,873 ZAR per night

Guest favorite

Bungalow in Winona

4.99 out of 5 average rating, 158 reviews

*Prairie Island Bungalow with Water Access*

Welcome to Prairie Island Bungalow (PIB)! Located on Prairie Island in Winona, this home provides the perfect, quiet getaway for work or play, and is your gateway to outdoor adventure in the Winona area. River access is available on our private dock next door! With thoughtful amenities including a fully-stocked kitchen (with coffee and tea!), plush linens, Smart TVs, games and books, a fire pit, snowshoes, and kayak and canoe rentals; we invite you to simply show up and enjoy your stay at PIB!

Aug 9 – 16

R4,739 ZAR per night

Guest favorite

Home in Fountain City

4.95 out of 5 average rating, 101 reviews

River Road Abode: breathtaking river views

Entire 2 bedroom home with amazing views of the Mississippi from every room in the house. 3 unique decks to watch birds, barges, boats, bluffs and trains. Out front you can wave at people passing by on the Great River Road. Located near WI and MN state parks, wineries, breweries, and restaurants. Adventure outdoors or stay in and watch all the Mississippi has to offer from the private patio and decks. Trains pass by property day & night. Home is well insulated & ear plugs are provided.

Feb 12 – 19

R3,428 ZAR per night

Guest favorite

Home in Winona

4.91 out of 5 average rating, 205 reviews

Winona, MN- Cozy 3 bdrm bungalow with river view

Our home/cabin is up along the bluffs allowing eagle eye views of the Mississippi River. A perfect quiet place to take everything in. There are three bedrooms intended for large families or group get-aways. Everything is at your fingertips from beaches, to hikes in the bluffs. It is 3 miles south of Winona. While you can see the river, there is easy access to public landing if you choose to bring a boat to partake in the various islands and water sports.

Jan 7 – 14

R2,483 ZAR per night

Guest favorite

Apartment in Winona

4.98 out of 5 average rating, 815 reviews

~ Third Street Suites ~ #11

Hi! This beautiful main level apartment is conveniently located in the heart of downtown Winona MN! Everything Winona has to offer is within close proximity. Examples include: Coffee, restaurants, a wine bar, Winona State University, Mississippi River, Lake Winona, hiking trails, Shakespeare Festival, Minnesota Marine Art Museum, and much more! Please allow us to make your next stay in beautiful Winona a memorable one!

Jan 6 – 13

R2,036 ZAR per night

Guest favorite

Tiny home in Winona

4.99 out of 5 average rating, 118 reviews

Potluck String Lodge (PSL)

Potluck String Lodge (PSL) is situated within Prairie Island Campground along the Mississippi River. With cottony sheets, coffee & towels, paddle sport equipment & bikes, and an outdoor fire ring, you can simply show-up, relax, reconnect, and recreate. This tiny house tells a story about the Boats and Bluegrass music festival and one of the campground picking circles hosted by the Potluck String Band.

Sep 16 – 23

R2,992 ZAR per night

Guest favorite

Home in Winona

4.96 out of 5 average rating, 109 reviews

Beautiful Views of the Mississippi river

This spacious 6300 sf home sits on 18 wooded acres and overlooks the Mississippi and is ideal for large groups. We can accommodate up to 14 guests. 5 bedrooms with 10 total beds. 2 kings, 3 queens, 5 twins. There’s also a pull out couch and additional mattresses. Large, fully stocked kitchen. 2 refrigerators and 3 large living rooms. Coffee maker and coffee. Sorry, No pets.

Feb 20 – 27

R7,400 ZAR per night

Guest favorite

Home in Winona

4.95 out of 5 average rating, 117 reviews

Spacious Retreat for 1-8 guests

Staying with us for work or pleasure, this tranquil home is sure to suit all your needs. It has been renovated with charm and comfort in mind. All the modern indoor amenities will make you feel at home. Outdoors, enjoy the fully fenced in yard for privacy. It is conveniently located near Winona’s outdoor recreation, shopping, hospital and more.

Sep 9 – 16

R3,933 ZAR per night

Guest favorite

Loft in Arcadia

4.98 out of 5 average rating, 120 reviews

Tamarack Point Homestead

Tamarack Point Homestead is located between Arcadia, WI and Centerville, WI in the beautiful valley of Tamarack. This scenic 150 year old homestead has an outbuilding loft that allows you to enjoy the country lifestyle and experience the best that Trempealeau County has to offer. Certified to operate by the Trempealeau County Health Department.

Jul 26 – Aug 2

R1,844 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Winona vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Winona's top sights

Prairie Island Campground3 locals recommend

Hy-Vee5 locals recommend

Bloedow's Bakery13 locals recommend

Bub's Brewing Co7 locals recommend

Acoustic Cafe15 locals recommend

Midtown Foods5 locals recommend

Other great vacation rentals in Winona

Guest favorite

Home in Arcadia

4.95 out of 5 average rating, 134 reviews

Sonney Lodge

Sep 2 – 9

R3,229 ZAR per night

Guest favorite

Cottage in La Crosse

4.93 out of 5 average rating, 577 reviews

Breezy Point Cottage

Mar 17 – 24

R1,855 ZAR per night

Guest favorite

Cottage in La Crosse

4.89 out of 5 average rating, 132 reviews

Cheerful Cottage Near the Bay

Aug 28 – Sep 4

R1,806 ZAR per night

Guest favorite

Cabin in Dakota

4.91 out of 5 average rating, 175 reviews

Secluded cabin in beautiful river valley.

Oct 30 – Nov 6

R3,045 ZAR per night

Guest favorite

Apartment in Trempealeau

4.97 out of 5 average rating, 101 reviews

Small Town Vibes with Amazing River & Bluff Views

Nov 16 – 23

R2,639 ZAR per night

Guest favorite

Guesthouse in Rochester

4.98 out of 5 average rating, 166 reviews

Hygge House | A Cozy Guesthouse~15 min from Mayo

Mar 4 – 11

R2,252 ZAR per night

Guest favorite

Barn in Hixton

4.88 out of 5 average rating, 229 reviews

A Suite Getaway

Oct 29 – Nov 5

R2,633 ZAR per night

Guest favorite

Home in Winona

5.0 out of 5 average rating, 11 reviews

The Little Train Depot

Jul 24 – 31

R1,671 ZAR per night

Show all

Other great vacation rentals in Winona

Guest favorite

Cottage in Winona

5.0 out of 5 average rating, 45 reviews

Cozy Casita by the Lake

Nov 23 – 30

R2,667 ZAR per night

Guest favorite

Cottage in Winona

4.92 out of 5 average rating, 61 reviews

Cottage by Lake Winona

Sep 24 – Oct 1

R2,854 ZAR per night

Guest favorite

Home in Winona

4.96 out of 5 average rating, 57 reviews

A Stone's Throw Bungalow

Sep 26 – Oct 3

R3,359 ZAR per night

Guest favorite

Tiny home in La Crosse

4.96 out of 5 average rating, 49 reviews

Come unwind with us at Kindred Tiny House.

Dec 2 – 9

R1,921 ZAR per night

Guest favorite

Home in Fountain City

4.97 out of 5 average rating, 71 reviews

Bluffside cottage with gorgeous river views

Oct 3 – 10

R3,509 ZAR per night

Guest favorite

Guest suite in Fountain City

4.98 out of 5 average rating, 40 reviews

Backwaters Bungalow: waterfront/next to state park

Jan 23 – 30

R2,389 ZAR per night

Guest favorite

Cottage in Winona

4.96 out of 5 average rating, 28 reviews

Esther’s Cottage

Aug 28 – Sep 4

R4,349 ZAR per night

Guest favorite

Home in Winona

4.98 out of 5 average rating, 51 reviews

Ellie’s Place

Jan 21 – 28

R4,393 ZAR per night

Show all

Quick stats about vacation rentals in Winona

Total rentals
70 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
6.4K reviews
Nightly prices starting at
R380 ZAR before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Winona?
Yes! Work meets play with ease at over 30 vacation rentals in Winona featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Winona?
Four-legged friends are welcome in Winona. Choose from more than 20 vacation rentals for guests traveling with pets.
Do house rentals in Winona have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Winona. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winona have wifi?
Absolutely! We offer over 20 house rentals with wifi in Winona. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Winona?
Winona has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Winona have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Winona. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Winona?
Experience the best of Winona with our apartment rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for House Rentals in Winona?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a bbq area, over 20 homes with air conditioning, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Winona vacation rentals

Top-rated vacation rentals in Winona

Vacation rentals for every style

Houses

Apartments

Cabins

Popular amenities for Winona vacation rentals

Stay near Winona's top sights

Other great vacation rentals in Winona

Home in Arcadia

Cottage in La Crosse

Cottage in La Crosse

Cabin in Dakota

Apartment in Trempealeau

Guesthouse in Rochester

Barn in Hixton

Home in Winona

Other great vacation rentals in Winona

Cottage in Winona

Cottage in Winona

Home in Winona

Tiny home in La Crosse

Home in Fountain City

Guest suite in Fountain City

Cottage in Winona

Home in Winona

Quick stats about vacation rentals in Winona

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Winona?

Are there pet-friendly vacation rentals in Winona?

Do house rentals in Winona have air conditioning?

Do house rentals in Winona have wifi?

Are there family-friendly house rentals in Winona?

Do house rentals in Winona have a bbq area?

How much does it cost to stay in apartment rentals in Winona?

What are the most popular amenities for House Rentals in Winona?

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